Basically, I'm assuming my current environment will continue (having fast Internet, and having Dropbox exist and have high uptime). It's not like I'm screwed if

Basically, I'm assuming my current environment will continue (having fast Internet, and having Dropbox exist and have high uptime). It's not like I'm screwed if one of these factors suddenly changes- all of my files are still on my computer and on my occasional hard drive backups. I would just have to find a different backup method or back up to my HDD more regularly. > backup to an offsite file-server that you also control This doesn't help with problems A, B, or C in your list. It's not like Dropbox uses an order of magnitude more bandwidth than an offsite fileserver. And in that case, I'm depending on my fileserver host to continue to exist. I'd also be relying on my own ability to configure and maintain a secure fileserver and keep it up-to-date with security patches, etc. While I can certainly do that, my time is worth money to me. I'd rather pay $10/mo to people who do it full-time for a living.